Greenville Upstate - Warfield & Company

From First-Time Buyer to Investor: What I’ve Learned from 100+ Personal Transactions

Real-world lessons from decades of buying, selling, and investing—to help you succeed in any market.

A handshake between business people, symbolizing successful property investment deals.

Buying your first home can feel overwhelming. Investing in your first property? Even more so. I know because I’ve been there—more than a hundred times.

Over the course of my career, I’ve personally bought and sold over 100 investment properties and lived through four personal home sales. Those experiences taught me lessons you just can’t learn in a classroom or a quick online search. Whether you’re purchasing your very first home or thinking about expanding into real estate investment, here are a few things I’ve learned that can help you move forward with confidence.

1. The Right Property Isn’t Always the Perfect Property.
When you’re buying a home to live in, it’s easy to get caught up in emotion. When you’re investing, it’s all about numbers and potential. Understanding the purpose behind your purchase—whether personal or investment—helps you stay focused on what really matters.

2. Timing Matters, but Preparation Matters More.
You can’t always control market timing, but you can control your readiness. The clients who succeed are those who have their financing lined up, know their goals clearly, and can act decisively when the right opportunity appears.

3. Renovation Isn’t Always a Goldmine.
Flipping houses looks glamorous on TV, but real life is messier. I’ve found that some of the best investments are the ones that needed minimal work and could hit the rental or resale market fast. Sometimes “good bones” are more valuable than a “blank slate.”

4. Relationships Are More Valuable Than Deals.
I’ve built a network of contractors, lenders, inspectors, and fellow investors who’ve helped me time and again. In real estate, your relationships are your superpower—nurture them.

5. Every Transaction Teaches Something New.
No matter how many deals I’ve done, every property has taught me a new lesson. Stay humble, stay curious, and always treat each transaction with the respect it deserves.

Whether you’re buying your very first home or eyeing your tenth investment property, I’m here to be a resource for you—sharing not just advice, but experience earned through years of real-world practice. Let’s build your future together.

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